4-Chloroindoline Chemical Properties

Boiling point:

135 °C(Press: 10 Torr)

Density 

1.214±0.06 g/cm3(Predicted)

refractive index 

1.603

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.26±0.20(Predicted)

CAS DataBase Reference

41910-64-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

2735

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2933998090

4-Chloroindoline Usage And Synthesis

Synthesis

GENERAL STEPS: The synthesis of 4-chloroindoline from 4-chloroindole was carried out as follows: 4-chloroindole (20.0 g, 148 mmol) was dissolved in acetic acid (60 mL), followed by the addition of sodium cyanoborohydride (18.7 g, 296 mmol) in batches. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was slowly poured into 1500 mL of a 2 M NaOH aqueous solution. The aqueous phase was extracted with dichloromethane (CH2Cl2) and the organic layers were combined. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to give 4-chloroindoline (20.0 g, 98% yield). The product was confirmed by 1H NMR (400MHz, CDCl3): δ3.08 (2H, triple peak, J=8.4Hz), 3.62 (2H, triple peak, J=8.4Hz), 6.62-6.66 (1H, multiple peaks), 6.78-6.83 (1H, multiple peaks), 6.90 (1H, double double peaks, J=7.6,0.4Hz).

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 5, p. 1649 - 1666
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1598 - 1612
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[5] Patent: US2008/27014, 2008, A1. Location in patent: Page/Page column 39

4-Chloroindoline(41910-64-9)Related Product Information

• Hydrochlorothiazide
• Clopidogrel hydrogen sulfate
• 4-Chloroindole
• Indole-3-butyric acid
• Indoline
• Indometacin
• cis-Octahydro-isoindole
• Indole
• Isoindoline
• Indole-3-acetic acid
• Difluorochloromethane
• 4-CHLOROISATIN
• 4,6-DICHLORO-1H-INDOLE-2,3-DIONE
• 4-Chloroindoline-2-one
• 4-Chloro-7-methylisatin
• 4,7-Dichloroisatin
• 5-CHLOROINDOLINE
• 1,3,3-Trimethyl-2-methylene-5-chloroindoline